Hydrogen chloride-ethyl acetate → Hydrochloric Acid

HRID 713182Notes

Reaction equation

HRID 713182 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[C:5]([F:23])[CH:4]=1)#[N:2].[ClH:24].CCOC(C)=O>>[F:23][C:5]1[CH:4]=[C:3]([CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:1]#[N:2].[ClH:24]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57933849HCID 57933849, compound

Product 2

HCID 313Hydrochloric AcidYield 36%HCID 23087388HCID 23087388, compound

Procedure

A solution of tert-butyl 4-(4-cyano-2-fluorophenoxy)piperidine-1-carboxylate (42 g, 131 mmol) dissolved in 4:1 HCl/EtOAc (100 mL) was stirred for 5 h. The mixture was concentrated to give the title compound as its HCl salt (12 g, 36%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.89 (m, 2H), 2.14 (m, 2H); 3.08 (m, 2H), 3.21 (m, 2H), 4.86 (m, 1H), 7.48 (t, J=8.4 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.89 (m, 1H); ESI-MS m/z [M+H]+220.7.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-e238f2f8fe2c4dc9884a07912677052c
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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